Pieces
by SweetCaroline9
Summary: Set at the beginning of season 4, Jenny Humphrey's return to the Upper East Side: how it should have been.
1. Chapter 1

Author's note: This is how I envisioned Season 4, and Jenny Humphrey's return, playing out. I'm not sure how long this story will be yet, I'm going to wait and see what people think of it.

Pieces

Chapter 1

Jenny took a deep breath, filling her lungs with crisp autumn air as she stepped off the train and onto the bustling platform. While there was a big part of her that immediately felt at home being back in the city, a bigger part had to remind her to breathe in order to keep her anxiety at bay. It had been almost a year since she left the Upper East Side, her old life, and the giant mess it had become. She had spent the last several months in Chicago at an innovative design school that allowed her to finish high school while prepping for a career in design. She loved Chicago, every part of it. It was so different there. It took a while, but for the first time in a long time she felt like she belonged somewhere. She had real friends and she wasn't suspicious of their motives or afraid they would turn on her for wearing the wrong shoes. She wished she was back there now. But instead, she was back in New York with a long fall break ahead of her.

"Jenny!"

She recognized Dan's voice. Glancing down the terminal, she saw her brother and father heading towards her, huge smiles on their faces. She smiled back and made her way towards them. They were the one thing she had missed about home. Well, and Eric of course.

"Oh sweetheart, I've missed you," Rufus said enveloping her in a big hug. He stepped back, not letting go of her shoulders. "Let me look at you. I barely even recognize you."

It was true. Jenny did look a lot different. The change had been gradual, but as things in her life had become lighter, more carefree, so had her look. Her hair was shorter, just past her shoulders, and a darker more natural looking blonde. Her face had barely any makeup, save for some concealer and mascara. Her outfit consisted of a long loose gray sweater over dark skinny jeans and navy Keds. She suddenly felt strangely simplistic compared to all of the edgy commuters in the busy train station.

"You do look great Jen," Dan said stepping forward for his turn. When he hugged her, Jenny squeezed him tightly, taking in his scent. She had missed her big brother more than she realized.

"You too Dan. Protesting barbershops I see," Jenny said when they broke apart.

"Very funny. I'll have you know longer hair is very in right now." Jenny and Rufus both shot Dan a quizzical look. "Nevermind."

"Okay, you two," Rufus interjected. "As much as I've missed your banter, the van der Woodsens are waiting for us so let's get your bags and get out of here."

"Sounds good," Jenny replied. She tried to sound excited but she could feel her anxiety rising.

Dan, seemingly hearing her thoughts, reassuringly grasped her hand as they headed towards the luggage area. At least distance hadn't dulled their psychic link, Jenny thought, as she clung to his hand like a lifeline.

* * *

><p>"Just promise you won't leave again, okay?" Eric mumbled, his face pressed into Jenny's shoulder. He had been hugging her for close to three minutes now and his death grip was making Jenny lightheaded.<p>

"Okay Eric. I promise, alright? Can you let go now?" Jenny responded, pain in her voice. Eric shook his head.

"Alright Eric that's enough. Give Jenny some breathing room won't you?" Lily said wearily.

Eric finally relinquished his grip and Jenny let out an exaggerated breath. She planned on looking annoyed but after months of phone calls and letters she couldn't keep the joy of being reunited with her best friend off her face. "I've missed you too," she said ruffling Eric's hair.

"Okay, watch the 'do," he responded stepping out of her each and smoothing a hand over his head.

Rufus and Dan chuckled. "It is wonderful to have you back Jenny," Lily said smiling warmly.

"It's wonderful to be back," Jenny lied. "Oh well," she thought. "No one will know." Dan tossed her a knowing glance. Well, almost no one.

Just then, the elevator dinged and Serena stepped out. She stopped when she saw Jenny. "Jenny, I forgot you were getting in today," she said. Her voice was neither warm nor cold, it just sort of…was.

"Hi Serena," Jenny said. An uncomfortable silence fell over the room.

"Well," Lily broke in, "I could use some help in the kitchen getting dinner together. Boys?"

"Don't you have a full-time chef?" Dan asked. Lily shot him a stern look. "I mean, I would love to help!" he said walking briskly out of the room followed by Rufus.

Eric didn't budge, his eyes darting between Jenny and Serena.

"Eric?" Lily asked.

"I'm good," he responded, now staring fixedly at Serena, doing his best impersonation of a guard dog.

"It's fine Eric," Jenny said, gently nudging him. He glanced at her, then back at Serena, before slowly turning and following Lily to the kitchen.

For a few seconds, silence hung between the two blondes. It was almost hard for Jenny to believe they were step-sisters and even harder to believe they had at one time been friends.

"Look, um, Serena, I'm really sorry about last year and how I treated you," Jenny said. "I really messed things up and I understand that you're probably less than enthused about my being back. I know I can't take it back and I don't expect us to be friends again or for you to even like me but I just need you to know that I am really really sorry."

Serena looked at the younger girl and smiled slightly. "It's okay Jenny. I mean sisters never really like each other right?"

Jenny smiled at Serena's attempt at diffusing the situation. She remembered why it had been so easy for her to like Serena in the first place. "Right," she said.

"Why is it so quiet in there? Is Jenny still breathing?" Eric shouted from the next room.

Serena rolled her eyes, "Now that you're back you can take my tactful little brother off my hands for a while," she said.

Jenny laughed as Eric and Dan walked in.

"What?" Eric asked.

"Nothing," Serena said. "I've got to get going, I'm meeting Blair for dinner."

"But I've prepared a celebratory dinner for Jenny," Lily said joining the group in the living room. "It's almost ready."

"You prepared it?" Eric asked, raising his eyebrows. Dan tried to suppress his laugh. Lily glared at her son.

"And…" Lily continued, "The charity gala is this evening and I'd like us to go together, as a family. It will be a great way to let our friends know Jenny is back home."

"Actually Lily, that was really nice of you but I'm beat. I think I'd just like to unpack and relax a little bit," Jenny replied. There was nothing she would like less than going to an Upper East Side gala on her first night back in town.

Lily was about to protest when Rufus stepped in. "That's understandable sweetie. I put your bags upstairs in your new room. Do you want some help unpacking?"

"Actually," Jenny began, "I wanted to talk to you about that." This was a moment she couldn't put off any longer. "The penthouse looks great and everything—"

"Thank you," Lily said, "Just wait until you see the size of your new closet."

"But," Jenny continued, "I was thinking I would actually rather stay at the loft with Dan."

Silence.

"Jenny…I don't think that's a good idea," Rufus said warily.

"Look, dad, I know I wasn't exactly responsible last year but you don't have to worry about that this time, okay? I just—I just don't…" Jenny trailed off. She couldn't exactly articulate that being around all of this high society stuff was toxic for her. Like being an alcoholic living above a bar. A bar with free booze.

Dan interjected, "I would be fine with me. Really fine actually. It would be nice to have to company…and someone to make me a sandwich every now and then."

Jenny elbowed her brother in the stomach and Rufus let out a small laugh. "Okay," he said uneasily. "We can give it a try. Tentatively."

"Thanks dad!" Jenny said hugging her father. "You won't regret it." She was so relieved.

"Jenny, are you sure I can't convince you to come to the gala?" Lily asked.

"Maybe the next one mom." Eric answered for her. "It's not like we have shortage of them around here."

* * *

><p>Jenny paced around the loft. She had finished unpacking two hours ago, Dan had left for the gala one hour ago, and Eric hadn't called to check on her in a solid thirty minutes.<p>

The loft was exactly how she remembered it. Records lining the living room wall, the smell of countless cups of coffee hanging in the air. In a huff of restlessness, Jenny threw herself down on the couch and stretched out. She wasn't exactly bored, just unsettled. She couldn't believe she was back here. Had it really been less than a year? It seemed like a lifetime ago. A lifetime that she would rather forget. The great thing about her school in Chicago was that there were always people around. Seldom was she left alone with her thoughts like she was now. These moments were when the darkness started to creep back in. When she felt that loneliness and self-loathing for the person she had become and the things she had done last year. She had told herself she was different now but she knew that wasn't how everyone else would feel. And what if they were right?

"Grrrrrrrrllllllllll."

Jenny's thoughts were interrupted by her stomach. In all the unpacking (and self-deprecating) she had forgotten to eat something. She stood up and walked to the fridge, opening the heavy door. Cheese, a half-eaten sandwich, and hot sauce were all that greeted her.

"Great Dan," she said, slamming the door shut. "Welcome back to living with a boy."

She grabbed her wallet and coat and headed out the door. At least she had an excuse for eating some junk food.

The walk to her favorite Thai place was chilly. She forgot how the temperature could change from day to night in the city. She picked up a steaming bowl of chicken pad thai and tipped the cook. She pushed the door open with her back a spun onto sidewalk. She walked a few steps, focusing on putting her change back into her wallet, when she slammed into someone, spilling coins everywhere.

"I'm so sorry," she said, not glancing up. "I wasn't watching where—"

"Jenny?"

Jenny froze. She knew that voice but wasn't ready to hear it quite yet.

"Nate. H-h-hi. Sorry I didn't see you." She stood up and they faced each other awkwardly.

"Dan told me you were coming home for the holidays," Nate said, rubbing the back of his neck. "When did you get in?"

"Today," Jenny said, "Just a few hours ago actually." Nate nodded.

It would have been easy to ask how he was, listen to his answer and then reply with something about her food getting cold and make a quick escape but Jenny knew that wasn't the right thing to do.

"Listen Nate, I never apologized to you for last year," Jenny began.

"Jenny, you don't have to—"

"No, I do. You were my friend, a good friend, and I took advantage of that. I'm really sorry…about everything," Jenny said meeting his eyes for the first time since they bumped into each other. They were just as bright and clear as ever.

"It's okay Jenny," Nate replied.

"No it's not, but thanks for saying that," Jenny said.

They stared at each other for a moment. Nate was taken aback by how normal she looked, like the Jenny he had spent the night talking to years ago, on Blair's birthday. It made him wonder how different he looked now, from the boy he was.

Jenny broke the silence, "Well, I should get going before my food gets cold. I'll see you around Nate." She said turning to leave.

"Wait, aren't you going to Lily's gala?" Nate asked.

Jenny looked down at her outfit, now complete with a pad thai stain, and smiled. "No, that's not really my thing."

Nate looked at her, confused. "Since when?" he asked.

"Since ever," Jenny replied. "It just took me a while to realize it." She smiled and walked away.

Nate stayed still for a beat watching her go before pulling his coat tighter and heading the opposite way.


	2. Chapter 2

Author's Note: Here is the next chapter. I know there hasn't been too much N/J interaction thus far but I promise the next chapter will be much more focused on them. Thanks for reading, leave me feedback to let me know what you think!

Chapter 2

"So you're telling me that in the entire city of Chicago, there hasn't been a single guy who has caught your eye?" Vanessa asked incredulously, tossing one of Jenny's dresses onto her bed.

Jenny rolled her eyes, "You asked if I was hooking up with anyone, not if anyone had caught my eye," Jenny replied.

It was Saturday afternoon and Vanessa had come over to the loft to borrow a dress for Serena's birthday party that night. Neither Jenny nor Vanessa could quite figure out why Serena had invited Vanessa but Jenny was happy to have the extra company. Afterall, she had successfully avoided any and all society events for the past two weeks but her step-sister's birthday party seemed inescapable.

"So there is someone! I knew it. Spill," Vanessa said, temporarily distracted from the task at hand.

"I've been there for nine months; I've gone on some dates. It's not a big deal," Jenny answered, trying to sound nonchalant but feeling anything but.

Vanessa raised her eyebrows but the blonde ignored her. Jenny was clearly trying to sidestep the conversation. If she wasn't in such dire need of an outfit, Vanessa would have pushed the topic further but she decided to let it drop…for now.

"So, uh, where's Dan?" Vanessa asked. Things had been a little weird since their whole semi-relationship and full-breakup last year but she was trying to get back to the way things used to be, with Dan and Jenny.

"He took Serena out to lunch for her birthday," Jenny responded. Dan and Serena were 'back on' and from what Jenny could tell, they were back to their typical star-crossed, destined-to-be relationship.

"Oh okay. Well I should get going. Tell Dan and Rufus I'll see them tonight," Vanessa said snagging a purple halter dress and walking towards the door.

"Okay, see you there," Jenny said. She laid back on her bed. Dan probably wouldn't be back to change for another hour or so and Rufus was already with Lily helping her set up for the party. It was being held in the grand ballroom of Chuck's hotel, which didn't go over well with Rufus…or Dan…or Eric. The three men in her life had pretty much founded the 'We Hate Chuck Bass Club' in her absence which was complicated by the fact that both Lily and Serena were just as loyal to him as they were before the 'incident.'

Jenny let out a loud sigh. She was NOT looking forward to being in the same vicinity as Chuck, or Blair for that matter. She had seen Blair briefly at the van der Woodsens' the week before and she was still pulling the daggers out of her back that B. had shot at her.

"Oh well," Jenny mumbled to herself. "Have to get this public humiliation out of the way eventually." She hopped up and began poking around in her closet for an acceptable outfit.

* * *

><p>When Jenny and Dan arrived at the hotel, the party was already in full swing. Lily had really outdone herself this time. The entire room had a golden glow which was perfected by a ten-foot fountain in the center of the room.<p>

"Beats renting out a bowling alley I guess," Jenny joked.

"Uhhhh, yeah," Dan replied, eyes wide. "I'm going to go find Serena. Are you okay?" he asked, giving Jenny's shoulder a light squeeze.

"Sure," Jenny replied. "You know me, I'll just go hang out by the refreshments."

Dan chuckled and walked off to find the birthday girl. Jenny looked around the room before spotting the bar and making her way towards it. Her dress swished against her legs as she walked. It was a light pink dress with a sweetheart neckline. Her outfit wasn't quite as glitzy as some of the other girls but she could take a full breath in it so she figured it was an even trade.

A diet coke was within reach when Blair's minions stepped into her path. Well, ex-minions, since Blair had graduated from Constance.

"Little J. We were wondering when you were going to surface."

"Yep," Jenny replied. "I heard there was free food." She tried to step around the trio but Nelly Yuki blocked her path.

"C'mon J, we've been dying to hear why you left. Just between us girls, what was it? Unwanted pregnancy, drug problem, DNA test confirmed Lonely Boy is in fact your real brother?" Penelope quipped.

Jenny was confused. Why were they acting like they didn't know about her and Chuck?

"All of the above I guess," Jenny replied. "Glad to see you girls are still bff's. See you in ten years!" Jenny pushed past the girls, ignoring the snarky comments they shouted after her. She let out a breath as she finally reached the bar, but she had lost her desire for a drink.

"Jenny! You look absolutely wonderful dear," Lily said as she and Rufus approached her.

"Thanks Lily. The party looks great," Jenny replied.

"What? This little thing. We really just threw it together, right dear?" Rufus joked, clearly teasing his wife for her extravagance.

"Yes, well, it is a special occasion," Lily replied.

Jenny smiled at Lily and Rufus. Her dad really did seem happy with Lily in her world. It's too bad Jenny hated it so much.

"I think I'm going to get some air," Jenny said, trying to excuse herself.

"Are you feeling okay sweetie?" Rufus asked, concerned.

"Oh, I'm fine," Jenny lied. "I'm just not used to so many people. I'll be right back."

* * *

><p>Jenny took a deep breath as she stepped out onto the terrace. It was a beautiful, clear night, as if even nature was acknowledging the sanctity of Serena's birthday. Jenny chuckled at the thought. Music from the ballroom wafted out into the night air and sounded soft and calming. Jenny closed her eyes and allowed the notes to lull her.<p>

"Enjoying the party?"

Jenny's eyes shot open and she turned towards Chuck, who was leaning against the railing on a portion of the terrace covered in shadows.

"Chuck," Jenny said tersely. "I didn't realize anyone was out here."

"Just enjoying the view," Chuck murmured, taking a step towards Jenny. Instinctively, Jenny stepped back and Chuck stopped. "That and hiding from some of my critics," Chuck admitted.

Jenny could tell he was talking about her dad but she didn't respond.

"You look good Jenny."

"Don't Chuck—" Jenny began.

"I didn't mean anything by it," Chuck replied, raising his hands defensively. "You look more like yourself is what I meant."

"Thanks," Jenny said, looking way. She did not want to be having this conversation. Her stomach turned just thinking about the last time she and Chuck were alone together.

Silence hung between them until Chuck broke in.

"Look Jenny, I don't know what to say."

"You don't have to say anything Chuck. Last year was a mistake but it was our mistake. You didn't force me to do anything, despite what my dad and brother may think."

It was true. Chuck had taken advantage of a younger, vulnerable, less experienced girl but he had been vulnerable too. And ultimately, she knew he hadn't meant for it to happen, or for Jenny to become so messed up as a result.

"Sure." Chuck said, not sounding completely convinced.

"Well, isn't this cozy?" Blair said from the doorway.

Jenny cringed hearing her voice.

"When you too are done with your date, it's time for Serena's cake." With that, Blair turned and walked back into the ballroom.

"Awesome," Jenny muttered before following suit. "Best. Night. Ever."

* * *

><p>About an hour later the party was winding down and Jenny was searching the room for Eric, her ride home.<p>

"You don't waste any time do you?" Blair asked, walking up behind her.

"There is nothing going on between me and—" Jenny began but Blair cut her off.

"I don't need details Little J." Blair said, hesitantly glancing around them.

Jenny paused. Blair seemed self-conscious, even more so than usual.

"I ran into your mini-me's earlier Blair. Imagine my surprise when they asked why I left town. I was sure Gossip Girl would have released a blast before I even boarded the train." Jenny stated watching Blair carefully. "You didn't tell anyone did you?"

"Like I would humiliate myself purposely," Blair snapped. "Chuck's poor taste reflects on me too you know."

"Look Blair, I know your pride is hurt, okay? But you have made it clear, repeatedly, that we are not friends. And you and Chuck were broken up, which had nothing to do with me. I have a list of people I owe apologies to but you're not one of them."

Blair stared at Jenny. Something was going on inside her head but Jenny couldn't quite tell what.

"You—"

"Blair!" Nate said interrupting her, "Serena is looking for you."

Blair looked at Nate, then back at Jenny. She turned and walked away without another word.

Jenny let out a breath she didn't realize she had been holding.

"Everything okay?" Nate asked, raising his eyebrows.

"Yeah," Jenny said, wanting to change the subject. Nate swooping in to rescue her was a pattern she didn't want to revisit. "Enjoying the party?" she asked.

Nate smiled, but before he could answer they were interrupted by a tall blonde.

"There you are," she said placing her hand on his arm. "I've been looking everywhere for you."

"Sorry," Nate said. "I was talking to Dan and Serena and then Serena asked me to find Blair."

"This isn't Blair," the blonde said jokingly.

"No, this is Jenny," Nate said gesturing towards her. "Jenny this is Juliet, my date."

"Nice to meet you," Jenny said, shaking Juliet's hand.

"You too," Juliet smiled. "Are you ready to go?" she asked Nate.

"Yeah, let's go. I'll see you later Jenny."

"Sure," Jenny said. "See you later."

Eric approached and offered Nate a smile as he and Juliet walked away hand-in-hand.

"Who is that?" Eric asked Jenny.

"Nate's date Juliet," Jenny replied. She suddenly felt exhausted. "Are you ready to go?"

"I was ready thirty minutes ago," Eric said. "I thought we were meeting outside."

"Ugh," Jenny threw her head back dramatically. "Let's get out of here."

Eric laughed as Jenny grabbed his hand and drug him towards the door.


	3. Chapter 3

Author's Note: I've been super productive today and the first few chapters have been really easy to write. You probably shouldn't get used to it :) Enjoy and review!

Chapter 3

"You're being ridiculous."

"What does Cedric have to do with anything?"

"Okay, I think that's a little excessive."

Jenny looked up from where she was sitting at the kitchen table as bits and pieces of Dan's telephone conversation drifted in from where he was in his bedroom. She had no idea who he was talking to but she had only heard him sound so exasperated a few times in his entire life.

"Okay, okay, fine. I'll be there in ten minutes. Bye." Dan hung up his phone and walked into the kitchen.

"Who was that?" Jenny asked, looking up from her magazine.

"That was, uh, Blair." Dan said quickly.

Jenny raised her eyebrows, "Blair?"

"Yeah," he replied. "It's a long story. I have to go meet her at the magazine. I'll be back."

"Okay…" Jenny said hesitantly, but Dan was already out the door.

Jenny finished reading the magazine and stood up from the table. She was going to meet Eric for coffee. He was going crazy being home with Lily all day and needed a distraction. While she was looking for her keys the doorbell rang.

Jenny opened the door and was surprised to see Nate.

"Nate, hey."

"Hey Jenny." Nate gave her a small smile.

"Um, Dan isn't here," Jenny said.

"Oh really," Nate said surprised, looking at his watch. "I thought we had plans at one."

"Well, something came up…I think. It was sort of last minute, he probably just forgot."

"Yeah…" Nate glanced around the loft.

"Is everything okay Nate?" Jenny asked. He was acting a little distracted.

"Yeah, sorry. What are you up to right now?" Nate asked, shifting his attention.

"I'm actually on my way out," Jenny said hesitantly. "I could, um, stay a couple minutes."

"No, no, it's fine. I'll see you later Jenny," Nate said leaving.

"See you," Jenny said watching him leave. She was confused, but she had been feeling that way a lot since being back in the Upper East Side. She tried to shake it off, found her keys, and headed out to meet Eric.

* * *

><p>"All I'm saying is that New York is like the design capital of the country. What does Chicago have, some giant mirrored ball thing?"<p>

Jenny laughed at her best friend. Conversations like this had been a constant occurrence pretty much since she stepped into the penthouse. Eric was determined—scratch that—obsessed with convincing Jenny not to go back to Chicago after break. It would be more endearing if his argument wasn't so absurd.

"It's called Cloud Gate, or 'the Bean' Eric," Jenny replied. "And who says New York is the design capital of the country?"

"People…everyone," Eric retorted weakly. "Don't act like you've never heard it."

Jenny shook her head. "You're right Eric, I'm never going back to Chicago. Why would I?"

"Really?" Eric asked, surprised.

"No." Jenny said getting up from their table. "Now stop it."

Eric groaned. He had another hour of arguing in him but he promised Rufus he would be back to help him fix Lily's armoire. Lily had wanted to hire someone to fix it but Rufus didn't think she should spend money on something the 'men of the house' could do. And hence Eric got roped in too.

"Fine. You win, for now," Eric said defiantly before smiling and kissing Jenny on the cheek. "I'll see you later…if your dad doesn't kill me with a nail gun."

Jenny laughed out loud at the picture—of her dad and the nail gun, not Eric dying.

"Call me later," she said.

"Okay, bye."

"Bye."

Jenny shoved her sunglasses onto her face as she stepped out onto the sidewalk. She didn't have any plans for the rest of the day so she thought a walk around the city sounded like a good idea, especially on such a nice day.

She had made it about two blocks when she realized she was nearing Chuck's hotel. She thought it better not to chance anyone seeing her even remotely close to anything related to Chuck so she cut down a side street about a block before the hotel, planning on by-passing the area altogether. She had only been a few feet when she recognized Mr. Archibald standing on the sidewalk ahead of her. He was stationary with his hands in his pockets, surveying the area. Maybe he was waiting for Nate? That didn't make much sense considering they were so close to the hotel where Nate lived and his father had been staying since being released from jail.

Jenny had met the senior Archibald a few times, usually just in passing. He seemed nice enough, always polite and friendly, but from what she had heard from Dan that was often a façade. Nate had been having a hard time with his father lately, especially with Mr. Archibald not taking his probation as seriously as he should.

Before she could get any more lost in her thoughts, a car pulled up to the curb where Mr. Archibald was standing and stopped. The driver rolled down the window and Mr. Archibald leaned over to peer in. The two spoke for a moment before Mr. Archibald extended his hand into the car and pulled it back out holding a small box which he quickly put in a bag he was carrying. And just like that, the car was gone and he continued walking as if the exchange had never happened.

Jenny put her head down and kept walking as he passed her, probably on his way back to the hotel. This is none of your business Jenny, she told herself. Just keep walking, forget it, it probably wasn't even what it looked like. She repeated these things over and over but they weren't sticking. She hated this city, hated how it made people act. What was he thinking? He was on probation for crying out loud! Was he thinking about his family? About Nate? Suddenly, Jenny flashed back to the conversation she and Nate had late one night before they even really knew each other. When he had told her about the pressure his dad was putting on him to keep up his relationship with Blair for the good of the family, even though that wasn't what Nate had wanted. She remembered the sad look in his eyes when he told her and something snapped inside of her. Jenny spun around and headed in the exact direction she was trying to avoid.

* * *

><p>"Can I help you miss?" the concierge asked.<p>

"Um yes. I was hoping you could tell me what room Howard Archibald is staying in?" Jenny asked. She was quickly losing her nerve but tried to push through it.

"I'm sorry, that kind of information is confidential. Is Mr. Archibald expecting you?"

Before Jenny knew what she was doing, she lied…big. "Yes, I'm Russell Thorpe's assistant and I'm just here to go over a few details of Mr. Thorpe's itinerary with Mr. Archibald." Then Jenny gave her biggest 'Don't I look like I could assist someone' smile.

"Let me confirm with Mr. Archibald," the concierge said before walking away to make a call.

Jenny let out a puff of air. "This is a bad idea," she mumbled to herself.

"He wasn't expecting you but Mr. Archibald said you could come up. He is in penthouse eleven," the concierge smiled.

"Thank you," Jenny said walking to the elevator. She was too wrapped up in her thoughts to notice the young girl snapping a photo of her with her cell phone.

She wasn't quite sure what she was going to say when she reached the eleventh floor. The elevator opened and she stepped out to face the front door. Taking a deep breath, she rang the bell.

Mr. Archibald opened the door, "Hello, can I help you?"

"Hi Mr. Archibald, my name is Jenny Humphrey, I'm a friend of Nate's."

"Of course, I remember you Jenny. Unfortunately, Nate isn't here and I'm actually expecting someone so I'll tell him you stopped by," he said beginning to shut the door.

"Actually," Jenny said, "I'm the person you were expecting."

"I'm afraid I'm not following," Mr. Archibald replied.

"I saw what you did on the street a few minutes ago," Jenny said, the softness gone from her voice. "How could you do that to your son?"

The older man blanched. "Jenny, why don't you come in so we can talk about this?" he asked gesturing inside the penthouse.

Jenny hesitated, she hadn't planned on coming in. "That isn't necessary," she said, "What I have to say is brief. After everything you have put your family through in the last two years how can you risk everything again. Nate deserves so much better than that." Jenny's face was flushed now, her previous feelings returning.

Mr. Archibald put his hands up defensively, "Jenny, I'm not sure what you think you saw—"

"What I did see," Jenny insisted.

He sighed. "I suppose I should be glad Nate has such a good friend. But Jenny, what you saw has nothing to do with Nate, or you for that matter, and I think you should just forget about it."

Jenny glared at him. Now she was really annoyed. "With all due respect Mr. Archibald, exchanging items on the side of the street with a car with tinted windows is not something people do when they have nothing to hide. It's definitely not what people on probation do. Nate has given you a second chance and you're throwing it away. I think you should tell him what happened today or I can tell him…and the police for that matter." Jenny said. With that she smiled and got back on the elevator, leaving Mr. Archibald standing in the hall, stunned.

* * *

><p>Jenny has just finished cleaning up the mess from dinner and was seriously considering going to bed at seven o'clock when someone started knocking on the door. She was once again surprised to see Nate on the other side.<p>

"Okay, you need to buy Dan a planner because he's in his room getting ready for his date with Serena," Jenny joked. Nate didn't smile.

"I'm not here to see Dan, Jenny," Nate said, his face hard. "I want you to explain this." He held up his phone and Jenny looked at it. It was a blast from Gossip Girl that read: 'It seems that our Little J. is graduating to the major leagues. She was spotted having an afternoon delight with one Mr. Howard Archibald. Looks like when the son is away the father will play.' Sure enough there was a picture of her in the lobby of Chuck's hotel.

Jenny was dumbfounded, Nate couldn't possibly believe that post. "Nate I can explain this," she began.

"Really? It must be an interesting story because I asked my dad if anyone stopped by today and he said he had been there all day without any visitors," Nate said. "I thought you were done with the games Jenny."

"Games?" Jenny asked. He did believe it. After everything that had happened, after all the apologies, Nate was standing in her living room accusing her of reverting back to her old ways when she hadn't even done anything! When all she had been doing was helping him.

If it had been anyone else, Jenny would have given them a piece of her mind. But suddenly she felt so defeated. She had fought so hard for Nate that day. Everything she had done had been for him, remembering the boy she had been so taken with that night on the steps. But just like everyone else, he believed the worst about her. She wasn't quite sure why it hurt so much more coming from him.

Jenny's eyes filled with tears but she refused to let them fall. "You know what Nate? Believe whatever you want," Jenny said, her voice cracking. She pushed past him, out of the apartment, so he wouldn't see her cry.

Nate just stood there. He wasn't sure what had just happened but he suddenly felt like maybe he had been a little rash with his reaction.

"Hey Nate, what's up?" Dan asked emerging from his room. "Where's Jenny?"

* * *

><p>Once Jenny was outside she realized she had left without a coat and it was pretty chilly outside. There was no way she was facing the humiliation that was waiting for her back upstairs though, so she just started walking.<p>

She made it about two blocks when she heard someone calling her name.

"Jenny! Jenny wait!" Nate shouted jogging up behind her. Jenny wiped at her face furiously to erase the tear stains that had formed there but she kept walking.

"Jenny, stop okay, I'm sorry," Nate said finally catching up with her and grabbing her shoulder.

Jenny turned towards him but wouldn't meet his eyes.

"How did you walk so far in less than two minutes," Nate asked, short of breath. Jenny didn't respond. Nate sighed and became serious, "Dan explained everything. I'm really sorry Jenny."

"It's fine Nate," Jenny said, trying to brush it off. "I'll see you later." She pushed past him, back in the direction they had come from, but Nate raced to cut her off.

"No it isn't. We can't just say 'see you later' this time Jen. You have to let me explain."

Jenny sighed. She was so tired.

Nate swallowed, looking at the ground. He was thinking about how to best phrase what he wanted to say. When he looked back up at Jenny she finally met his eyes.

"You've been so different the last few weeks. Happier, more…you. It's like I have my friend back," Nate began. "So when I got that blast and my dad lied about it, I felt like that was all slipping away. And I got angry, really angry. I jumped to the worst conclusion because, I guess that's what I've been afraid of since you got back. That I would lose my friend again."

Jenny's face softened. Nate continued, "I should have trusted you and I'm sorry."

"It's okay Nate," Jenny replied.

"No it's not. But thanks for saying that," Nate said smiling. Jenny smiled back, remembering their conversation a few weeks ago.

"I'm really glad you're back Jenny. I missed you and I should've told you that the first night I saw you."

On the surface he meant he had missed her since she left for Chicago, but Jenny knew that deep down he had been missing her for much longer.

"I missed you too Nate," she echoed.

They stood there for a minute just looking at each other before Nate spoke up.

"We should probably get back to the loft," he said. "Dan was pretty confused when I left."

Jenny chuckled, "It runs in the family."


	4. Chapter 4

Author's Note: Here is the next chapter. I know it's a little short but the next one is going to be a doosey! Enjoy and review!

* * *

><p>Chapter 4<p>

If you had told Jenny Humphrey six weeks ago that she would have slipped seamlessly back into her old life in New York, she never would have believed you. Okay, so it wasn't exactly seamless or her "old life" really, but she had weathered her first run-ins with Serena, Nate, Chuck AND Blair and was still alive to talk about it. She had even had a semi-break-down/break-through with Nate and their friendship seemed to be back on solid ground for the first time in years. Each day Chicago moved further out of her mind, and if it wasn't for a few special friends from school, she may have forgotten about it completely.

"I'm not saying I don't want you to be friends with her Dan. Just don't expect me to be so naïve as to believe Blair has really forgiven me for last year."

It was Tuesday afternoon and the Humphrey siblings plus Nate were sitting in the kitchen of their loft having lunch. It was strange, but the three of them had been hanging out like this a lot lately and per usual they found their conversation turning to the topic of Dan's unlikely friendship with the Queen B.

"How do you even know that? I've told her you've moved on and I'll have you know that the scathing comments have been less and less frequent," Dan said, quirking an eyebrow. Nate just listened silently, amused. "Jenny. Are you even listening to me?" Dan asked when Jenny didn't respond.

She wasn't. Her phone had buzzed when Dan was midsentence and Jenny was now fully engrossed in reading the message she had received. A smile spread across her face unconsciously, which both boys noticed before she had a chance to cover it up.

"Who is so important?" Dan asked, clearly annoyed.

Jenny snapped back to reality. "No one," she covered. "I have to make a call. I'll be right back." She escaped to her room before her brother could give a cynical response.

"Girls," Dan said, looking at Nate for agreement. But Nate was staring at Jenny's closed door, wondering who Jenny had been in such a hurry to talk to. He hadn't seen her smile like that in a long time.

Nate didn't even register Dan's voice until he had finished speaking.

"Sorry, what?" Nate asked. Dan just stared at him. Unbelievable.

Jenny emerged from her room ten minutes later to find Nate alone in the kitchen finishing his sandwich.

"Where's Dan?" she asked.

"Where do you think," Nate answered, a small smile tugging at his lips.

"The magazine? Again?" Jenny sighed, rolling her eyes. "We were supposed to go to the Cooper-Hewitt Museum today. They're having this great exhibit on 18th Century European textiles. We've been planning it for weeks."

"I'll go with you," Nate offered.

Jenny straightened, "You don't have to Nate."

"No, no it sounds interesting," Nate lied.

Jenny raised her eyebrows, "Don't you have plans with Juliet today?" she asked. She had tagged along with Nate and Juliet twice in the last two weeks and it was two times too many. She liked Juliet, she hated being the third wheel.

"Yeah, but they're just tentative," Nate said. "I'll just text her and let her know something came up." Jenny still hesitated. "Seriously Jenny, don't make me beg you to let me look at textiles with you."

Jenny laughed at this, "Okay," she conceded. "Let's go."

* * *

><p>The exhibit was great, everything Jenny had imagined it would be. As such, she knew Nate was bored out of his mind the whole time, which was why she proposed they get ice cream after, as a sort of unspoken reward for his patience.<p>

"So…" Jenny began. "How are things going with Juliet?" Talking to Nate about his love life wasn't her favorite thing to do but it was what a friend would do. She figured he could use the ear considering Dan was so wrapped up in his weird "whatever it is" triangle and Chuck was always working.

"Good," Nate said chuckling. "They're good."

Jenny smiled. "Why are you laughing?"

"Nothing, that was just really random," Nate answered.

"No it wasn't," Jenny argued. "You've been dating for what? A month? A little more? You should be able to say how things are going by this point."

"You're right," Nate said. It was still weird, Jenny asking him about Juliet.

"Besides," Jenny continued. "Not that I'm the authority, but she seems like a perfect match for you."

"In what way?" Nate asked. He like Juliet but had never really thought of them as similar.

"Oh, you know," Jenny said, pausing to take a bite of mocha chip. "Educated, well-spoken, _perfect_." She smiled as she said this last word. She was joking, but at the same time, not. "And I could see her sitting down for an Archibald family Thanksgiving and fitting right in."

"You don't have to be perfect to fit in with my family Jenny," Nate countered.

"Yeah," Jenny said. "But you do have to be comfortable with that world."

Nate stopped at this. "What world?"

"Your world," Jenny explained. "The Upper East Sider's world. High society, balls, country clubs." She looked at Nate. She shouldn't have to explain this to him. Afterall, he was the one who lived in it.

Nate furrowed his brow, "I guess I thought there was only one world and we all lived in it," he said, clearly becoming annoyed.

"I'm not trying to make you angry Nate," Jenny said, realizing she may have overstepped but not knowing how.

"It's fine," Nate said continuing to walk. "I guess I know what you think of me now."

"Nate, stop it," Jenny said. She put her hand on his shoulder and he stopped walking. "You know that's not what I meant. You're the only good thing about it."

They stared at each other as their ice cream continued to melt. Jenny suddenly felt self-conscious and removed her hand. "Besides," she said, "It's not like my world is perfect either."

"But you couldn't see yourself anywhere else?" Nate asked, his eyes meeting hers.

"I don't know," Jenny answered, not understanding why he was asking.

That was where the conversation ended. The next second, Nate got brain-freeze, Jenny laughed, and it was like the mention of worlds and where they belonged had never happened. For the next moments, they belonged right where they were.


	5. Chapter 5

Author's Note: New chapter! Review if you feel so led. Thanks for reading :) I hope you like it.

Chapter 5

Blair tapped her foot impatiently against the metal leg of the corner table she was sitting at. Nothing annoyed her more than lateness…that and the fact that the person she was waiting on was Dan Humphrey. There was a time when the thought of meeting Dan anywhere, much less in a public place, would have made her skin crawl. Lately, however, a strange thing had been happening. Although it took her a while to admit it, Dan was actually an asset to have at the magazine. Worse than that, she found herself seeking out his company over things non-business related. They had less than nothing in common, save for a love of movies, and his very lifestyle disgusted her. Nevertheless, she couldn't bring herself to distance herself from their unlikely friendship, which was why she was sitting in this Manhattan coffee shop…fuming.

Checking her watch again, Blair let out a loud sigh. The young couple at the table next to her glanced over but she ignored them. Any couple in matching plaid shirts clearly didn't merit her attention. She contemplated leaving, and then decided on calling Dan with a final warning.

She was rummaging through her bag for her blackberry when she noticed a familiar couple outside the window. At first she assumed it was Nate and Juliet but then the blonde he was with threw her head back in laughter and Blair recognized her…Jenny Humphrey.

Her eyes narrowed. Jenny and Nate were walking down the sidewalk, oblivious to anything going on around them. Nate had his hand on the small of Jenny's back and was whispering something to her. Jenny was laughing hysterically and shoved Nate away from her playfully. Blair watched them carry on this way until they stepped into a small café further down the block.

Blair was revolted. She was of course over Nate, had been for a while now, but even she felt he deserved better than that weasely little wannabe. What was he thinking? He couldn't really have forgotten everything she had done last year— she had made fools out of all of them.

Her thoughts were interrupted when Dan rushed in, out of breath.

"Sorry I'm late, I overslept and then I couldn't find my shoes and, well, things really just went downhill from there…" Dan trailed off, noticing the look of death on Blair's face. "C'mon Blair, it's only fifteen minutes," he said shrugging.

"Don't flatter yourself Humphrey," Blair said, rolling her eyes. "I practically forgot we were even meeting."

"Good to know," Dan said pulling out a chair.

"Anyway!" Blair said, ignoring his comment. "The real reason I'm upset is that my eyes are still burning from a repulsive PDA session I just witnessed between Nate and your little sister."

"Nate and Jenny are here?" Dan said looking around.

"They were outside," Blair said. "Although you would think they were in a hotel room from how they were acting." She took a sip of her soy latte.

"Okay, Blair," Dan said, "There is nothing going on between Nate and Jenny. Besides," he continued, raising his eyebrows, "Would it matter if they were?" He looked at her questioningly.

"Of course it would!" Blair said loudly. "Jenny ruined my life; the last thing she deserves is to be happy with another one of my exes."

"Your life isn't ruined Blair," Dan sighed. "In fact, I would say it's been going pretty well lately." He stared at her.

Blair broke his gaze, taking another sip of her latte. "If you're referring to our little movie dates, you can get over yourself Humphrey. And speaking of dates, how is Serena?"

"She broke up with me." Dan said matter-of-factly.

Blair sputtered, shocked by both his statement and its delivery. "What? Why? When did this happen?"

Dan attempted to flag down the waitress, "A few days ago. She said she didn't think we were 'meant to be,' whatever that means." He gave up, clearly not making any progress, and turned his attention back to the brunette across from him. "It's not a big deal. We've broken up before."

"Right," Blair said hesitantly. She couldn't help but fear that all the time she had been spending with Dan may have had something to do with this. "I suppose it was only a matter of time anyway. After all, she's uptown and you're Brooklyn," Blair said smirking.

"Thanks for putting it into perspective," Dan said sarcastically. Suddenly he became serious, "Really though Blair, you have to get over your issues with Jenny." He reached out and placed his hand over hers. "I'm glad we're friends Blair, I never thought I would say that but I am. But Jenny's my sister and we can't be friends if you try to make trouble for her."

Blair snatched her hand away, ruining the moment, "I'm a mature working woman now Humphrey. I've graduated from all of that high school drama." She smiled but inside her head the wheels were turning. Jenny had stolen Blair's happiness last year and now it was time to return the favor. First there was just the matter of digging up enough dirt to get the job done.

* * *

><p>Jenny was in a foul mood. Tomorrow was her birthday and somehow Lily had talked her into throwing a party tonight to celebrate. It had started out small but now there was a guest list a mile long and the location had to be moved from the penthouse to the grand ballroom of the downtown Hyatt. It wasn't so much the details of the party that were bothering her however. It was also the fact that she hadn't heard from some of her friends back in Chicago, one in particular, who she was sure would have called her by now for her birthday. She also had to deal with the fact that Dan had convinced her to invite Blair, who he was sure had had a change of heart in recent weeks. And to top it off, she was standing in the middle of Bergdorf's, being fitted for a beautiful dress which she had no desire to wear…ever.<p>

"C'mon Jen," Eric said sympathetically. "You look great."

He was right. The dress was stunning and it fit Jenny like it was made for her, but with all the things that had been going wrong, she felt anything but pretty.

"Fine. Can I take it off now?" Jenny asked the seamstress. She didn't want to seem ungrateful. In fact, the only reason she was going along with all of this in the first place was because it was important to Lily. Lily had been so good to her, even during all of her bad behavior last year, so she figured this was the least she could do.

Eric was waiting for her after she changed.

"Want to grab lunch?" he asked. "My treat…to celebrate."

Jenny smiled. Eric loved birthdays. Why wouldn't you when you had grown up doing them as big as all of the van der Woodsens did.

"Come on," he said, putting an arm around his best friend's shoulders. "It'll be fun. I'll be there and mom, Rufus, Dan, Nate…"

"It's okay Eric," Jenny said. "You don't have to convince me. I'm sure it will be fun." Jenny glanced down at her phone. "I've just been feeling a little out of sorts lately, that's all."

"Well, get in sorts!" Eric said enthusiastically. "You're going to need your energy up. After all, it wouldn't be an Upper East Side party without some fights, hook-ups, and shocking secrets coming to light." He jokingly clutched his chest and Jenny laughed.

"Good thing I don't have any shocking secrets."

* * *

><p>Jenny tried going into the night with an open mind and Eric had been right, she was having fun! Although there were A LOT of people at the party, Lily had done her best to keep it casual. There was lots of delicious food (all of which Jenny could pronounce), dancing, and even a slideshow of her younger years which was embarrassing but made her feel very loved.<p>

There had been two major highlights of the evening: first, a three-way dance off between Dan, Nate and Eric which left Jenny's stomach sore from all the laughing. Second, aside from a cordial greeting at the beginning of the night, she had successfully avoided Blair for the duration of the party.

Jenny was trying to appease a group of high society well-wishers when Nate made his way over, stealing her away, for which she was grateful.

"I haven't officially wished you a happy birthday," Nate said smiling at her. "Happy Birthday Jenny." He leaned in and kissed her gently on the cheek, lingering just a moment before pulling away.

Jenny made a face, wiping a hand down her neck. "Yuck! You are sooooo sweaty," she laughed. Her smile showed she really didn't mind. Nate smiled back.

"You're just jealous of my moves," he said, breaking into an awkward little two-step. Jenny threw her head back in laughter which only encouraged him. Nate grabbed her hand and twirled her around in front of him. She was laughing so hard that she wasn't prepared to stop and slammed clumsily into him, but Nate steadied her. Jenny took a deep breath, her cheeks flushed and a smile still on her face. Nate brushed a piece of hair out of her eyes. They began to sway to a soft song that was playing.

Jenny wrapped her arms around Nate's neck. "I'm sorry Juliet couldn't make it," she said.

Nate shrugged, lacing his fingers behind Jenny's back. "It's not a big deal; we really haven't been spending much time together lately. She's been really busy."

Jenny tilted her head to the side, "It sounds like you just need to work a little harder, that's all…if she's important to you."

Nate looked down, "Actually, I wanted to talk to you about that."

"About what?" Jenny asked.

"About, uh—" Nate was interrupted as Lily and Rufus wheeled out a giant pink birthday cake. The duo separated.

"Happy Birthday sweetie," Rufus said kissing Jenny on the top of the head and wrapping her up in a big hug.

"Thanks dad," Jenny replied.

All the guests gathered around and sang "Happy Birthday" as Jenny blew out the candles. The caterers began serving the cake but Jenny wasn't that hungry so she settled for stealing bites of Eric's piece.

"You could get your own you know, there's a whole cake over there," Eric said, feigning annoyance at the third bite Jenny stole.

"I don't want my own piece," she countered. "I just want to share yours," she said sweetly, batting her eyes as Eric tried to shield his plate from her.

Nate chuckled at the two.

"Has anyone seen Blair?" Dan asked, joining the group.

"Not since earlier," Eric said.

At just that moment, the music cut-out and Blair's voice came over the sound system. She was standing in the center of the room holding a microphone.

"Before everyone leaves for the evening, we have one more surprise for the birthday girl."

Jenny swallowed. This could not be good. Dan had already begun making his way towards Blair but she continued, "Here is a special surprise from all of your friends in Chicago!" She gestured towards the door but all anyone could see was a young man with brown hair and a shy smile making his way into the room.

It took a second for Jenny to make out what Blair was pointing to but when she saw him a huge smile spread across her face. "Matt?"

The boy smiled wider, finally seeing Jenny and rushed towards her. Jenny did the same and he swept her into his arms, twirling. Jenny laughed out loud as he spun her. He set her feet back on the ground and before anyone had a chance to ask what was going on, he kissed her.

The room was silent. Dan, Rufus and Eric had no idea what was going on. Rufus didn't like that some strange guy was kissing his daughter and Nate didn't like that Jenny was kissing him back. What was she doing? Who was this guy? Nate blamed the anger he was feeling on his protective side but deep down he knew his feelings weren't exactly brotherly.

Jenny had gotten so caught up in the moment that she forgot where she was or more importantly how many other people were there. She broke away from Matt but he was still grinning like an idiot which made her smile back—it was contagious. However, the smile didn't last when the embarrassment and confusion began to set in. Jenny pulled Matt aside and was relieved when the music came back on and people began to disperse.

"Happy Birthday," Matt said touching the side of Jenny's face. She closed her eyes momentarily, reveling in how much she had missed him before snapping back to reality.

"Matt. What are you doing here?" she asked. Chicago was too far away for this to be a chance visit.

"Your friend Blair invited me," he explained. "She thought it would be a fun surprise."

Jenny grimaced. She had already forgotten that Blair had been the one who had announced Matt's arrival, who had set this all in motion. But how had she found out about him? Jenny hadn't even told Dan about Matt. And what was her angle? It wasn't like bringing Jenny's super cute friend/boyfriend/acquaintance-of-an-undefined-manner to town was really the most devastating thing Blair could cook up.

Matt noticed the change in her demeanor. "It is okay that I'm here right? I mean your friend said—"

"She's not exactly my friend…" Jenny interrupted. She really did not want to go into her history with Blair right now considering she hadn't told Matt about anything that happened last year. In fact, she had pretty much only told him the bare essentials of her life in New York. Suddenly, she was seized with panic. What had Blair told him? Was that what this was all about? Airing her dirty laundry in front of the most important person in her "new life."

"Jen?" Matt asked. Now he was the one who was confused. "What's going on?"

Before Jenny had time to answer, or think of an answer, Rufus walked over. Her was followed closely by Dan, Nate, Eric and Lily.

"Jenny, who is this?" Rufus asked. Eric had that guard dog look on his face again and Nate…well Nate had a look on his face that Jenny couldn't quite figure out but she didn't have time to worry about that right now.

"Dad, this is my, um…this is Matt," Jenny said stumbling over her words. She suddenly felt like she was a six-year-old about to be reprimanded by her father. She was reassured by Matt stepping forward, placing one hand on the small of her back and extending the other towards Rufus.

"It's nice to meet you Mr. Humphrey," he said, shaking Rufus's hand. "I've heard a lot about you."

"That's ironic, we've heard nothing about you," Dan quipped.

Jenny shot him a look, "Matt, this is my brother Dan. I've told you about how he can be." Dan made an offended face but Jenny continued down the line. "And this is my best friend, or well step-brother Eric. And my step-mother Lily. And this is Nate." Jenny wasn't sure why she didn't give him a label like the others. "Everyone, this is Matt. We go to school together in Chicago."

"It's a pleasure to meet you Matt," Lily said, always the picture of class. "Chicago is quite a ways away; I hope your trip went well."

"Very well," Matt said, looking down at Jenny. "Time flew by." Jenny blushed. Nate shifted uncomfortably.

"What brings you to New York so unannounced?" Rufus asked, clearly still wary of Matt.

"I wanted to surprise Jenny for her birthday," Matt explained.

"So," Eric finally spoke up, and gave a voice to what everyone was thinking, "Are you two like, dating?" He was annoyed that this information had been kept from him.

"Okay," Jenny broke in. "That's enough with the questions for now. It's late, I'm sure Matt is tired," she said turning to him. "Maybe we should call it a night and we can all talk more tomorrow." She desperately wanted time to debrief him before he faced the firing squad.

"Just a minute," Rufus said sternly. "He will not be staying at the loft, I don't think so."

Jenny rolled her eyes but before she could make a bratty comment Matt spoke up, "Actually, I have a friend who lives in the Soho area so I'm going to stay with him while I'm in town. I have a rental car, can I give you a ride home first?" he asked Jenny.

"Yes," Jenny smiled. "I'm beat anyway," she said turning to Lily and Rufus. "Thank you for the party. It was great." She hugged them both. "I'll be fine," she said pulling away from Rufus.

"Call me as soon as you're home," Rufus said. "And Matt, we'll see you tomorrow morning for breakfast." This was really more of a demand than a question.

"Sounds great," Matt said. He was always an optimist, that or just really dense. Either way, it was something that had first attracted Jenny to him. "It was nice meeting all of you," he said.

"Dan, do you want to come with?" Jenny asked her brother.

"No. I, uh, need to have a conversation with Blair," he said, rubbing the back of his neck. Jenny gave her brother a sympathetic smile. She had tried to warn him but a part of her felt bad for Dan. He really had believed the best in Blair.

"Okay. Love you all," Jenny said as Matt took her hand and led her towards the door. She mouthed "I'll call you later" to Eric as he shot her an incredulous look. They were about halfway to the door when Jenny stopped.

"Shoot!" She said. "I forgot something. Meet you outside?" she asked.

"Sure," Matt said, kissing her on the cheek. "I'll pull the car around."

Jenny smiled as he left. She didn't have the heart to explain that everyone around here used valet. She turned and scanned the room, spotting Nate alone at a table at the other end of the room.

"Hey," Jenny said, walking up and making him jump. He had clearly been lost in thought.

"Hey," Nate said. "I thought you left."

"I am…we are," she said glancing in the direction Matt had gone. "But I didn't want to leave without talking to you first."

Nate raised his eyebrows. "Talking to me?" he asked.

"Yeah," Jenny explained. "Earlier you said you needed to talk to me about something."

"Oh yeah," Nate said, understanding what she was referencing even though she really didn't. "I, um, just wanted to say, uh…happy birthday."

Jenny smiled, "You already said that."

"Right," Nate said smiling back. "Well I really mean it." He paused before continuing, "You're really important to me Jenny."

Jenny lost her smile. Suddenly the moment felt much more serious. "You're important to me too Nate," she said. She stepped towards him, enveloping him in a hug. Nate lowered his face to the crook of her neck, breathing in her scent. All too quickly, Jenny pulled away. She smiled at Nate. "I'll talk to you tomorrow, okay?"

"Yeah, talk to you then," Nate replied, forcing a smile which he held until Jenny had reached the door and disappeared outside. Then he slumped back down in his chair.

"I hate Upper East Side parties."


	6. Chapter 6

Author's Note: Hey guys, sorry it has taken me FOREVER to add a new chapter. Hopefully people are still reading. Enjoy!

Chapter 6

Jenny strummed her fingers on the countertop and checked the clock for the fifth time in the last four minutes. She was alone in the loft waiting for Matt to pick her up so they could drive to the penthouse for brunch. Dan had left a little while before, fed up with Jenny's constant pacing, although he claimed it was to make sure everyone was on their best behavior before the couple arrived.

Jenny couldn't believe how nervous she was. There was something unsettling about her life in Chicago crashing so abruptly into her life in New York. Not that she was worried about her family accepting Matt himself. He was one of the most charismatic guys she had ever met. He had this ability to put people at ease which was what drew her to him in the first place…not that she had made it easy.

The first time Jenny met Matt it had been her first day at her new school in Chicago. She arrived a few days before the semester began and was trying to get situated in the dormitory-style room she had been assigned to stay in with a peppy brunette named Amber. Amber was in her second year at the school and had plenty of friends so Jenny was left alone to unpack on her first Friday night in the new city.

She was simultaneously blaring the Ramones, feeling sorry for herself and her pathetic life, and folding sweaters when someone knocked on the door. Before Jenny had a chance to answer, the door swung open, revealing a tall, brown-haired boy wearing a bright green 4-H t-shirt.

"Hey, did you order a pizza? 'Cause there's a guy downstairs demanding $12.50 for a deep-dish pepperoni and there are only a couple of us here, and I've pretty much checked with everyone else so…"

Jenny stared at him incredulously. "Have you ever heard of knocking?" she demanded. She felt all of the tension in her body that had built up over the last few days shooting out of her eyes and directly at the intruder.

Matt gazed at her for a few seconds and then broke out into a huge grin, which only made Jenny angrier.

"Sorry," he said. "Usually I'm worried about someone being naked or having sex when I knock and I've never heard of anyone being in the middle of either of those with music playing that loudly." He kept smiling, clearly amused.

Jenny didn't know which infuriated her more: that this guy she didn't even know had barged into her room, or that he clearly wasn't put-off by her angry look and dark makeup like everyone else she had encountered thus far.

"The volume of my music doesn't give you the right to barge into my room," Jenny bit out. She was quickly becoming unnerved by the way he was staring at her with the same smile on his face. "Besides," she added, "maybe I like having sex to loud music." She delivered this line completely stone-faced. That should do it, she thought, proud of herself.

"Good to know," Matt replied nonchalantly. "So do you want a slice?"

"What?" Jenny asked, confused. He had deflected her sex comment like it was nothing and now she had no idea what he was talking about.

"Do you want a slice?" Matt repeated. "…of pizza. I'm not completely convinced you didn't just order it as a way of getting me to come up here and introduce myself but I'll be the bigger man and foot the bill…just this once."

Jenny could have sworn he actually winked at her as he said this. Was he joking? "That's ridiculous," Jenny said. "I would have had no way of knowing you would even come up here."

"You're right," Matt agreed. "I guess it is a little far-fetched. You're probably more of a salad girl anyway." He turned to leave her room. "Oh and it's Matt by the way," he added.

Jenny looked at him. On one hand, she was seriously considering throwing something at his head, but on the other, she was slightly impressed that a boy with a Midwestern accent would be so unbothered by her bad attitude and ripped fishnets.

"Jenny," she finally said.

"I guess I'll see you around Jenny," Matt said.

"Sure," Jenny replied. "And Matt?" He turned to face her. "The next time you want to say hi, you don't have to make up some lame pizza story to do it."

That made Matt smile, really smile.

Jenny's trip down memory lane was interrupted by a knock at the door. She practically leapt up to answer it. Matt was standing on the other side, giving her that same happy grin he had the first time she met him.

"Am I late?" he asked. "You look kinda annoyed."

Jenny smiled shyly. "Not annoyed," she said. "Just a little nervous."

Matt threw his arm around her shoulders and led her into the hall. "Don't be nervous, I've been going over some of my best jokes. They're going to LOVE me."

Jenny groaned as Matt laced his fingers through hers. This was going to be a long day.

* * *

><p>Jenny was relieved that Matt had been kidding about the whole joke thing. Not that it mattered, both Serena and Lily found every word that came out of his mouth to be absolutely hilarious. Even the men seemed to be warming up to him, with the exception of Eric who kept the same hesitant look on his face throughout most of the meal.<p>

Aside from the constant questions from her father, things were going pretty smoothly. Matt explained how he had moved to Chicago from Ohio when his father got a job there. The transition had been rough but it had helped him realize that he had a passion for graphic design, which had led him to the school and consequently, Jenny. Then of course they all wanted to hear how the couple had met, although Jenny gave the paired down version, altogether eliminating the sex comment. They were all stuffed and finishing up with coffee when the topic of conversation changed to their plans for next year.

"So Matt, you and Jenny have both earned enough credits to receive your high school diplomas. What are you going to do next?" Lily asked politely.

"I actually got accepted to SAIC and they have openings this spring. We're really excited," he replied.

"We?" Eric asked suspiciously.

Matt glanced at Jenny who was doing her best examination of the inside of her coffee cup. "Yeah…" he said slowly. "Jenny was accepted too. You told them, right Jen?"

Jenny looked up. "I meant to, I just hadn't yet." She looked at her dad. "I got accepted to the School of the Art Institute of Chicago." She smiled hesitantly. "Surprise!"

"That's great sweetie, congratulations." Rufus smiled but it didn't quite reach his eyes.

"Yeah Jen, that's a great school. We're proud of you." Dan added, squeezing her shoulder from where he was sitting next to her. "But I thought…I mean, I guess we kind of all assumed you would be coming back to New York once you received your diploma."

Jenny didn't know what to say. When she first came back to the city, she had been dreading it. She felt like she had pretty much made up her mind that Chicago was where she wanted to be. But now, being back with her friends and family, she realized that this fit too. She didn't know how to respond in a way that would satisfy everyone she cared about.

"I don't know. SAIC is a really great school and I haven't heard back from Parsons. Spring isn't for a little while anyway so…"

"You applied to Parsons?" Matt asked. This was new information to him as the couple had only ever talked about starting SAIC together.

"Um, yeah." Jenny replied. "I was going to tell you, I just…"

"Why wouldn't she apply there? Parsons is the best design school in the country." Eric interrupted. He could not believe Jenny was actually considering staying in Chicago. Sure they had argued about it over the last few weeks but in the back of his mind he had just thought she was being stubborn and would eventually give in.

"Eric…" Serena interjected. "I'm sure it's not an easy decision. Calm down."

"I am calm," Eric replied defensively. "It just makes sense that Jenny would want to be where all the most important things in her life are."

"And all the worst." Matt added.

The table fell silent. Matt didn't know all of the details of why Jenny left New York but he knew that it was bad enough that she refused to tell him about it when they shared everything else in their lives.

Jenny's head was spinning. This conversation had spiraled out of control. If she was confused about what she was going to do before, she definitely had no clue about what to do now.

"I need some air," she said, excusing herself from the table.

"Jenny, wait." Matt said, standing. "I'm sorry. I shouldn't have—" But Jenny was already out the door.

"I'll check on her." Dan said, following his sister. Matt sat back down, a defeated look on his face.

Jenny sucked in a big gulp of air as her feet touched the sidewalk. Although it was much louder on the busy street, she instantly felt calmer away from the questioning stares and awkward silence of the table. She heard her brother clear his throat behind her. She turned to look at him, expecting a sarcastic remark to break the tension but instead Dan just held out his arms and she walked straight into them. Immediately she started to cry, not a lot, just little sniffles. Dan tightened his grip on her and smoothed her hair. After a few minutes she calmed down, stepping back and wiping the tears off of her face.

"How's my makeup?" she asked.

"A big improvement from last year," Dan replied jokingly. Jenny punched him in the arm. "Ow!" he said, feigning pain. "See if I ever run after you again."

Jenny smiled. Dan always knew how to distract her from her problems.

"What should I do Dan?" She asked. If anyone knew how difficult coming back to New York had been for Jenny it was her big brother. Afterall, he had been the one constantly warning her about the evils of the Upper East Side. If only she had listened.

"I don't know Jen," he said, draping one arm around her shoulders. "But whatever you decide, you know we'll all support you."

"Even Eric?" she asked.

"Maybe after he gives you the silent treatment for the first few months." Dan smiled sympathetically.

"Hey." Matt said softly from behind them as he stepped out of the building.

"Hey." Jenny said, smiling slightly.

"I'll leave you to it." Dan said, kissing Jenny on the forehead and walking back inside.

The two stood in silence for a few minutes. "Look Jenny, I'm really sorry," Matt began. "I shouldn't have said that, about the bad stuff. I'm just a little confused okay? I thought I was coming here to surprise you and we would get to spend some time together and then I find out the girl who invited me has some kind of vendetta against you and now you're not even sure if you're going to come back to Chicago? It's all just a little much."

"I know," Jenny said. She felt tears stinging her eyes again but blinked them away.

Matt stepped forward and lifted her chin. "I'll be honest. The only thing that has gotten me through the past few weeks and you being away is knowing that you'd be coming back. When that became uncertain, I guess I just got defensive."

Jenny met his eyes. "Matt, I know there is a lot that I need to tell you and it isn't fair that you have to be in this situation and dealing with all of my baggage—" her voice cracked.

"Jenny," Matt said, wiping away a stray tear. "I've never asked you to tell me because it doesn't matter what happened before we met. The girl I fell for is the girl I met in Chicago. Whatever happened to get you to that point is just water under the bridge." Jenny smiled, Matt had always been this way with her but it still always felt surprising.

"I want you to do whatever makes you happy. And while I selfishly want you in Chicago with me, I also honestly think that's where you're happiest. I know you were in a dark place at the beginning of the year and you're so different now, and I think that's because you love Chicago."

"And because of you," Jenny added.

Matt smiled sheepishly. "We'll make it work okay? Whatever you decide."

"Okay," Jenny agreed. She didn't have any extra clarity on the situation but she was relieved that she hadn't ruined the one good thing that came out of her running away to Chicago.

"We should go back up so I can say goodbye to your family." Matt said.

"Yeah," Jenny said. "Let's go."

* * *

><p>Jenny didn't get back to the loft until 10:30 that night. She had spent the rest of the day after brunch showing Matt around the city and doing her best not to think about the future. He had decided to head back to Chicago in the morning. He didn't come right out and say it but Jenny knew he was cutting the trip short because he didn't want to add any stress to her life by being there. She had tried to convince him to stay for a couple more days but he very sweetly (as usual) declined. He told her he would see her in three weeks, when break was over. Whether or not that would be in Chicago, Jenny wasn't quite sure.<p>

She walked into the kitchen and threw her keys on the counter. There was a note from Dan explaining that he went out for a little bit and would be back later. Normally, she would have just assumed that he was with Blair but he was pretty upset with her since they had spoken at the party and Blair admitted that she invited Matt to New York to humiliate Jenny by telling him all about last year. Of course this didn't happen seeing as Dan had completely ended their friendship that night after she told him and surprisingly, Blair had backed off.

Jenny suddenly felt physically and emotionally exhausted. She changed into a pair of boxer shorts and one of her dad's old Lincoln Hawk t-shirts and plopped down on the couch. She felt like she should wait up for Dan but based on how heavy her eyelids felt, she wasn't sure that would happen. She was starting to drift off when there was a knock on the door.

"Nooooo." Jenny whined. She got up with a sigh, not certain she could take any more surprises. She was relieved when Nate was on the other side of the door.

"Hey," she breathed out. She was really glad to see him after the day she had had.

"Hey," Nate replied. "Are you okay? You look like you don't feel well."

"Thanks," Jenny laughed, stepping aside so he could come in. "Is giving me an ego boost the only reason you're here?" she asked sarcastically.

"I didn't mean it like that." Nate said. "You know I always think you look great." Jenny blushed, caught off-guard by his comment. He quickly changed the subject. "So, uh, how was brunch?"

"Good," Jenny said. "But also a disaster."

"Yeah," Nate said. "I talked to Dan earlier, he filled me in."

"Right," Jenny said. She wondered how Nate had reacted to the possibility of her returning to Chicago, not that he would care.

"Well I'm sick of talking about it. Tell me something to take my mind off of it." She said, returning to her seat on the couch. Nate followed suit, sitting beside her.

"I broke up with Juliet," he said abruptly.

Jenny was shocked by his sudden omission. "Oh. I'm sorry," she said. "I guess a lot has happened since last night for both of us."

"Yeah," Nate smiled. "Especially in our love lives." He was attempting to lighten the mood but the truth was he was surprised and strangely disappointed by the fact that there was a new man in Jenny's life. Not that he had expected her to abstain from dating while in Chicago, but in all the time he had known her, she had really only had one constant love interest…him.

Silence hung between them.

"You should hang out with Matt sometime," Jenny said quietly. "I think you would really like him."

"I bet." Nate said. "Maybe we can do something while he's in town." Jenny was quiet. "Or not," he continued, interpreting her silence negatively. "I mean we don't have to. I'm sure you want to spend as much time with him as possible."

"It's not that," Jenny assured him. "He's actually leaving for Chicago tomorrow morning."

"Oh," Nate said. "He misses deep dish pizza that much, huh?"

Jenny chuckled, "Yeah, something like that. What about Juliet? Why did you guys break up?"

"We just weren't connecting," Nate said. He paused. "Actually that's a lie." Jenny looked at him questioningly. "I broke up with her because I think I have feelings for someone else and it wasn't fair to lead her on." Jenny just stared at him. Nate swallowed, trying to muster all of his courage. "You know how, sometimes, there are people in our lives who we always seem to come back to?" Jenny nodded. "But after a while it seems like things haven't worked out so many times that it would be stupid to take another chance on it?"

"Yeah," Jenny said, smiling slightly. "I do."

"Really?" Nate asked, hopeful.

"Of course." Jenny replied. "Look Nate" she put her hand on his arm, "I think you should tell Serena how you feel."

Nate's face fell.

"I know you two have a long history and she really hurt you last summer but if being with her is what could make you happy then you have to at least try."

"Jenny—"

"That's how it was with me and Matt."

Nate stopped what he was saying and Jenny continued. "Last year I was a mess. With Damien, then throwing myself at you…and Chuck." Jenny's cheeks flushed at the memory. "I had completely sworn off men. But then I met Matt, and while it took a lot of convincing on his part, I opened up to him and took a chance on love again, and it's been great…he's been great. I feel good about myself again, and it's been a while since I could say that."

Nate was quiet. Jenny had completely misinterpreted what he was trying to say. Her eyes had lit up when she was talking about Matt in a way he had only ever seen when she was with him. He should have been happy for her as a friend, that she had finally moved on. But he only felt utterly dejected.

"You're right Jenny," Nate lied. "Maybe I will tell her. Listen I've got to go okay?" he said standing up.

"Sure," Jenny said, walking him to the door. The stopped in front of it and Jenny got up on her tip-toes to kiss his cheek. "Any girl would be lucky to have you," she said. "Remember that, okay?"

"Okay," Nate said "Goodnight Jenny."

"Goodnight," she said, closing the door behind him.

Nate stood outside the loft staring at the closed door for a few seconds. Then he shoved his hands in his pockets, preparing for the cold walk home.


	7. Chapter 7

Author's Note: Here is the next chapter. Leave me some feedback and let me know what you are thinking about the story so far! Thanks and enjoy!

Chapter 7

Jenny hadn't realized that seeing Matt again, albeit only for a short period of time, would make her miss Chicago and her friends there so much. However, she found that the process of making one of the most important decisions about her future to date was a good distraction.

She had spent the past week going back and forth between her two prospective design school programs. She had already sent her deposit to SAIC, figuring she would rather hold the spot and chance losing the money, but Parson's was also breathing down her neck for an answer and she still hadn't chosen between the two.

This is how Jenny's week had gone: the first day was spent listening to Celine Dion (which she hid from her father—he would not approve) and drowning her sorrows over Matt leaving in junk food. Day two she swore off men and the emotional turmoil they cause which pointed her towards New York. Day three she saw Nate and Serena together at a coffee shop in Manhattan which suddenly made Chicago look a lot better. Days four and five were spent with Eric and those conversations were too lengthy to even describe. Day six Jenny had a serious "Agnes" moment and decided she was over design altogether, which she thought could be celebrated by lighting some of her most recent sketches on fire in the kitchen garbage can. Dan had to wrestle the lighter away from her and then strongly advised her to "stop drinking the Kool-Aid." This brought her to today, day seven. She was at the loft with Dan, mainly because he didn't believe she was mentally capable of being alone.

"We could get Thai food?" Dan suggested. The two were discussing lunch choices. For some reason, neither of them had ever become inclined to go grocery shopping more than once a month.

"Nah. I still feel sick from all the garbage I ate earlier this week," Jenny replied, referring to her "mourning" period.

Dan's phone rang. He looked down at the screen before putting it on silent and shoving it in his pocket.

"Okay," he continued, ignoring the call. "How about that new vegan place on Fifth?"

"Maybe," Jenny said. "Who was that?" she asked, pointing to his pocket.

"No one," Dan said, getting up from his seat at the counter and walking into his room. "Maybe we should just skip dinner. It's already sorta late. We could just grab frozen yogurt?"

Jenny wasn't convinced by his nonchalant attitude. "Sure," she hollered. "Seriously, why won't you tell me who was on the phone?"

Silence.

"I know you can hear me Dan, your bedroom wall is a garage-door, remember?"

Dan reemerged. "It was no one, I told you." He walked around her to the living room but she followed him.

"How does 'no one' dial a phone?" Jenny asked sweetly.

Dan gave her an annoyed look. "It was Blair," he said shortly.

"Oh." Now Jenny felt bad. She knew Blair had been a sensitive subject lately.

"Look, Dan, if you're freezing her out because of me, it's okay. You can be friends with her. I'm over it, I promise," Jenny said, crossing her heart.

"It's not okay Jenny," Dan replied. "She was deliberately trying to hurt you."

"Yeah but what else is new?" Jenny said. "That's how Blair is, you know that."

Dan was silent for a moment. "Yeah but I just thought…I don't know. I thought maybe it was different this time."

"Why would it be different?"

"I just thought I had gotten through to her, that's all," Dan said.

"Well then, I guess it's good that you've cut your losses," Jenny said, trying to be positive. "And you can move on. Besides, you were just friends. It's not like you were dating and she broke your heart or something that would really do damage."

Dan sat still, avoiding Jenny's eyes.

"Wait." Jenny said slowly. "She broke your heart?" This could not be true.

"Okay, okay," Dan said defensively. "Heartbreak is a little extreme. I may have…possibly…I mean, it's a possibility…that at one time, I could have had more than friendly feelings for her."

"I can't believe you are in love with Blair Waldorf," Jenny said.

"Jenny..." Dan warned.

"Are you only going to give your babies first initials instead of full names?" Jenny joked.

"I'm leaving," Dan said, brushing past her.

"Wait," Jenny laughed, grabbing his arm. "I'm sorry but it is a little comical."

Dan wasn't laughing. "I mean serious. It's very serious," Jenny corrected, but couldn't stop grinning.

"Okay, I'm glad you find my life so humorous," Dan said.

"Oh I do, I really do," Jenny replied. "You better be nice to me or I might have to send out a Gossip Girl blast."

"Don't even joke," Dan said. "Besides," he added, "Nate already threatened me with that."

"You told Nate?" Jenny asked in an offended tone.

"Yeah last night." Dan said. "We had an early celebration since I can't make it tonight."

Jenny turned white.

"Celebration?" she asked.

"Yeah…" Dan said. "You know, The Captain gave Nate a seat on his company's board. It's like the biggest honor an Archibald can receive." Jenny just stared at him. "His parents are having a party to celebrate in their suite tonight, remember? You RSVP'd right?"

Jenny smacked her forehead. "I completely forgot that he called me! I've been so distracted the past week." She felt awful, and self-centered, and like a jerk.

"Man, at least I've been working. What's your excuse?"

"A NERVOUS BREAKDOWN!" Jenny shot back. She ran to her room and quickly changed, while Dan sat back down at the counter. He was amused that the spotlight had shifted from his bizarre romantic pursuits to Jenny's negligence.

"Okay," Jenny said hurrying back into the kitchen and grabbing her purse and keys. "I'll go over early and apologize for being MIA over the past week, maybe help set up?"

"If he lets you in." Dan said.

Jenny glared at him. "Have fun at the magazine," Jenny countered. "Tell Blair I said hi." She slammed the door before he could respond.

* * *

><p>"Congratu—" Jenny stopped mid-sentence as she peered past Nate into his apartment. "—lations? This doesn't look very party ready." She said.<p>

"That's because there isn't a party," Nate responded, walking back to where he had been sitting in the living room. "I told everyone on the guest list already."

Jenny glanced at the floor, and then followed him inside. "I know," she said. "I'm a terrible friend. I've been really wrapped up in my own stuff. I forgot to call you back. Dan just told me the good news." She smiled hesitantly. "It is good news right?"

"Of course it's good news," Nate replied coolly. "I'm the youngest person who's ever been offered a seat."

"Right," Jenny said, sitting beside him. "Then why aren't your friends here celebrating with you?"

"I don't know," Nate said. "None of the people who I really care to celebrate with could make it."

Jenny's cheeks became warm with shame. He had to be talking about more people than just her, right? She hadn't been a very good friend lately but it's not like her presence would have made or broken the party.

She leaned back in her seat, mimicking Nate's position, and let out a sigh.

"Buy you a pizza?" she asked.

Nate continued to look forward but smiled slightly. "Sure."

* * *

><p>Two hours, seven slices, and one Marlon Brando movie later, Nate and Jenny were lazily sprawled across his giant living room. Nate was stretched out on the floor while Jenny was taking up the whole couch.<p>

"That was definitely not the cinematic masterpiece you said it would be," Jenny said, yawning halfway through her sentence.

"Hey!" Nate said, playfully tossing a pillow at her. "Don't insult a classic okay? Besides you said this was my celebration and I could pick, so don't start complaining now."

Jenny smiled. "I wasn't complaining," she said sweetly. "I was sharing my opinion." With that, she lifted the pillow above her head and brought it down on Nate's face with a "thud."

"Oh, you are SO dead," Nate said standing up and grabbing Jenny by the waist. Jenny tried to squirm out of his reach but he was too strong. She gasped for air through her laughter as he mercilessly tickled her.

"Stop…Nate….please," Jenny laughed.

"Do you give up?" he asked.

"Yes, yes…I give up…just…stop."

Nate smiled mischievously. "Say Marlon Brando is the master."

Jenny held her breath and struggled harder.

"Never," she said.

"Say it."

"He's not."

"Say it."

Now Nate was almost fully on top of her. Jenny was stubborn, but she knew this was a battle she was not going to win.

"Okay…Marlon Brando is the master," Jenny mumbled.

Nate grinned and sat back. "I knew you really liked it."

Jenny propped herself up on her elbows and cocked an eyebrow. "You're so full of it," she said, but she was grinning widely.

Nate leaned forward and brushed a piece of hair out of her eyes. Jenny was sure she looked like a mess after that whole tickling episode but with Nate she never felt like she had to worry about that.

Suddenly, she was very aware of just how close Nate's face was to hers. His eyes were bright and clear as they stared back at her. She would have sworn this was one of those moments when the stars aligned and the guy leaned in for the perfect kiss. That is, if he wasn't Nate and she wasn't Jenny and they didn't have the friendship they had.

The moment was interrupted when Nate realized what an awkward position they were still sitting in, Jenny laying back on the couch and Nate straddling her thighs. He shifted to the side and swung his leg over hers before helping her sit up.

"Sorry," he chuckled nervously.

Jenny smiled. The duo sat back against the couch. Jenny was still slightly winded but enjoyed the comfortable silence. Sometimes she wished it could be like this all the time, just the two of them, no pretense, no problems.

Without turning her head, Jenny asked, "So you're going to sit on the board then? It's official?"

"Yeah," Nate said. He sighed and Jenny wondered if he felt the same way about their little bubble.

"It's because you want to, right?" Jenny said. "Not because of your family?" Nate turned to look at her but Jenny continued to look forward. She was almost afraid to look at him, afraid to see anger on his face. She remembered the last time they talked about him and his family, their world, and she didn't want to revisit that.

"I know how you feel about my family Jenny." Nate said. He continued before she could protest. "My grandfather has a lot of faults but he's smart and good at what he does. It's a great opportunity."

Jenny was quiet.

"Sometimes," Nate continued, "you have to go with your head, even if you heart is somewhere else."

Jenny finally looked at him. Once again, she was transported back to that night so many years ago when she had seen the "real" Nate for the first time. They were so different now, both individually and together. A lot of things had changed for Jenny since her freshman year: her friends, her look, her school. One thing that never seemed to change was Nate. No matter what had happened between them, he was always there, just being Nate. Now, in this moment, with Nate's words resonating in her mind, she fully felt the weight of growing up. That things were going to be different, Nate with his new job and her with design school. Jenny knew when she left for Chicago last year that she was starting a new chapter of her life, and ending an old one. What she hadn't expected was to come back and regret that.

Nate smiled at her, like he had so many times before, and she smiled back. But inside, it all felt different.

* * *

><p>Jenny shut the door as quietly as possible and crept into the loft. A light clicked on in the living room, making her jump.<p>

"Dan!" she breathed. "You scared the crap out of me. Why were you sitting in the dark?" Dan was weird but sitting alone in the dark living room well past midnight took things to a new level.

"Just thinking," Dan said, rising from his seat and stretching. "How was the party?"

Jenny plopped her purse on the counter. "Didn't happen," she said. Dan gave her a quizzical look but she just waved her hand. "It's a long story," she said.

"Here," Dan said picking an envelope up off the counter and holding it out towards her. "It was outside earlier. It's from Parson's."

Jenny took the envelope and glanced down at it for a moment before setting it back down.

"Aren't you going to open it?" Dan asked.

"No," Jenny replied. "I don't need to."

Dan raised his eyebrows. "Sounds like you finally made a decision."

"Yeah," Jenny said. "I'm going back to Chicago."


	8. Chapter 8

Author's Note: Sorry this chapter has taken such a long time to write but here it is! I've really enjoyed writing this story. Thanks so much to everyone who has reviewed! Enjoy :)

Chapter 8

Two months ago, there was nothing Jenny wanted less than to be back in New York. She started the countdown to her return trip to Chicago pretty much the minute she stepped off the train. But now, here she was sitting in a café with Eric, spending her last day in the city with her best friend. Strangely, this day had come much faster than Jenny could have imagined. Even stranger was how sad she was to see it arrive.

Of course, these sad feelings were fleeting. At least, that's what she kept telling herself each time her eyes began welling up when Eric mentioned her dad, or Lily, or Dan, or the loft, or Cedric, or late night pizza, or…well you get the picture. But she was making the right choice, the mature choice, she was sure of it. Afterall, Nate's words were still imprinted in her mind, like a stamp on her brain that says "It's time to grow up."

"Sometimes, you have to go with your head, even if you heart is somewhere else."

And he was right. Jenny loved New York, but maybe it was like an old pair of shoes that you love the look of but can't really fit into anymore. Isn't that what life is like anyway? A continual cycle of trends, the shedding of one style or phase for another. Clearly, she had been spending too much time thinking about design school.

Jenny's inner monologue was interrupted by Eric gently touching her hand from across the table.

"Jenny?" he said, searching her eyes for signs of life. "Did you hear what I said?"

"Oh sorry," Jenny apologized. "I got lost in a thought."

"I see you are really savoring our last moments together," Eric said. It was meant to be a joke but it came out with more of an air of sadness than either of them had been expecting.

Eric didn't remove his hand but rather tightened his fingers around hers.

"I'm really gonna miss you," he said softly.

Jenny felt her eyes begin to well up. "Really?" she asked. "So you're not going to spend the next six months hating me and ignoring my calls.

Eric smiled slightly. "I could never hate you," he said. "And if I ignored your calls, who would I talk to when our family is being crazy."

Now Jenny smiled. She didn't realize how much she had missed Eric while she had been away until she was reunited with him, things falling right back into the way they used to be. They had had their share of problems last year, but when push came to shove, Eric had been there for Jenny in a way no one else was.

"What are you going to do for the rest of the day?" Eric asked, finally breaking their connection to check his watch.

Jenny exhaled, puffing out her cheeks. She wiped at her eyes to erase any tears which may have escaped.

"Well," she began. "I said goodbye to Lily last night and I was with Vanessa right before this, so I'm going to go home and finish packing then I was planning on going over to Nate's to say goodbye to him and Serena. Dad and Dan are going to take me to the train station after."

"Why is Serena at Nate's?" Eric asked.

Jenny shrugged. "Why are they ever together?"

She felt like it went without saying: Nate and Serena, Serena and Nate. The golden couple. It was the natural flow of things for them to get back together. Eric could be so clueless sometimes.

"Are you sure you don't want me to come to the station with you?" Eric asked as they stood up from the table.

"Considering it took twenty minutes to get you off of me when I got back from Chicago, I would rather not make a public scene and watch you get removed by security at the station for holding a passenger hostage."

Eric laughed, slinging an arm around her shoulder as they stepped out onto the street.

"Well, those security guards can be pretty cute." He said, as they continued on their way.

* * *

><p>Jenny was about halfway done packing when she had a visitor.<p>

"Nate," Jenny said, surprised. "What are you doing here? I thought I was meeting you later."

"Well, I was in the neighborhood," Nate said, walking past her into the loft. "Thought I'd stop by, see if you wanted to grab a coffee or something."

"Oh," Jenny replied. She glanced around the loft and all of her belongings intermixed chaotically with half-packed bags and a few boxes.

"I'm just sort of in the middle of packing," she said. "I really can't take a break right now."

"C'mon Jenny," Nate said, flashing her a smile that faltered when she didn't return it. "What's an hour or two, right?"

Jenny wasn't sure why Nate was acting so nonchalant about her schedule. He knew her train was leaving that night and it was obvious she was nowhere near ready to go.

"I can't Nate," Jenny said. She felt bad but she really needed to finish packing. She was also afraid that one last coffee date with Nate would break her resolve.

"I have an idea," she said. "Why don't you stay and help me. It could be fun, there are lots of embarrassing memories in here waiting to be uncovered." She smiled, but it didn't quite reach her eyes.

Nate just stood there for a moment. "So you're really going?"

Jenny was taken aback. "What do you mean? You know I am."

Nate looked straight into her eyes, the way he always seemed to, but this time it was unnerving…like she didn't want to know what was coming next.

"I need to tell you something," he said. His voice was clear and determined.

"Okay…" Jenny replied.

"I don't think you should go back to Chicago," he said.

Jenny took a deep breath. "Nate, we've talked about this. Chicago is where I live now, I go to school there. I have to go back." She paused and then added, "It's time to grow up."

"What about New York?" Nate asked, now a slight edge to his voice. "What about everything you said before, about missing your family? Your friends?"

Jenny's face softened. "Nate," she said softly. "Look, no matter where I am, we're still going to be friends." She reached out a touched his arm. "Okay?"

"I don't want to be your friend," Nate said.

Jenny pulled back as if she'd been slapped. Her face hardened. Now she was annoyed. Leaving was hard enough and Nate was the last person she had expected to make it harder—purposefully at least.

"Then I don't even know why we're having this conversation," Jenny said, moving to walk past him and open the door. Before she could pass him, Nate grabbed her arm, stopping her and forcing her to face him.

"Jenny, that's not what I meant." She wouldn't meet his eyes but he dropped his hand so that it trailed down her arm and eventually encircled her hand.

Nate took a deep breath. "I meant that I don't want to _just_ be your friend."

"Nate…" Jenny said, a look of confusion on her face.

"We've never been 'just friends' Jen," Nate continued, his grip on her hand tightening. She didn't pull away and he took this as a reason to keep going. "There has always been something there. You're the one person who, no matter how hard I try, I've never been able to walk away from."

"But Serena—" Jenny interjected.

"I don't have feelings for Serena," Nate said softly.

Jenny just looked at him. So he hadn't been talking about Serena that night.

Nate stepped closer to her. He touched his hand to her cheek. "Jenny…" he whispered before leaning in towards her.

Suddenly Jenny stepped back, breaking their connection.

"What are you doing?" she demanded.

Nate was confused. "I told you," he said. "I don't want you to leave. I want to be with you—"

"You're ruining everything." Jenny said. "You can't just show up the night I leave for Chicago and tell me all of this."

"So I should have just let you go without telling you how I feel?" Nate asked incredulously.

"Yes…I mean no…ugh!" Jenny sighed. She rubbed her hand over her face, trying to collect her thoughts. "I'm with Matt now Nate. I care about him."

Nate stepped towards her and grabbed her hand again. "You can't tell me what you have with him is like what we have." He said.

"What we have is a friendship," Jenny said.

Nate rolled his eyes in frustration. "Come on Jenny, it's more than that. Think about everything we've been through."

Jenny looked down at her feet.

"I am thinking about it," she said softly before lifting her eyes to meet his. "I remember what it felt like to be in love with you Nate. Years of wanting you, years of unrequited feelings. And I can't be that person again." She swallowed the lump that had risen in her throat. "It would kill me."

Nate searched her eyes, desperately wanting to find the right words to reassure her. All he could think to say was, "I won't let that happen to you again Jenny. I promise." He swallowed before adding, "I love you Jenny. Always have, always will."

Jenny just looked into Nate's eyes, wishing with everything in her that she could believe him. That she could believe that this was the moment that everything over the last three years had led to.

"I'm sorry Nate," Jenny said. "I can't."

"Jenny…" Nate began, but he could see in her eyes that she couldn't be convinced.

Jenny knew it too. That broken part of her, the part that she had tried so hard to heal, was still big enough to be a reminder of the darkest part of her life. A part of her life that she never wanted to relive. In so many ways, Nate represented everything that was good in her life, all the best parts of who she had hoped to one day be. But at the same time, it was her desire to be that person, and to be with Nate, that had ultimately driven her into the darkness. And because of that, she just couldn't chance falling into that world again.

"I think you should go," Jenny said quietly.

Nate let out a breath. He felt like he had been punched in the stomach. Slowly he turned towards the door. He took a few steps before he paused. Without turning back to face her he said softly, "What you said before…it was never unrequited Jenny. Never." And with that, he was gone.

The sob that Jenny had been suppressing escaped her lips as she sunk in a heap onto the floor.

* * *

><p>It took a good 40 minutes for Jenny to process, meaning cry hysterically, what had just happened with Nate. By the time she pulled herself together she had trails of mascara running down her face and a massive headache. She called her dad to let him know that she was running behind schedule and would just meet him at the train station. Then she washed her face, pulled her hair back into a ponytail, tried not to think anymore about Nate Archibald, and finished packing.<p>

She had just zipped up her last bag when there was another knock on the door.

"Nope," she mumbled to herself. "Not doing it. Nothing good can come from this." She was fed up with visitors. But the knocking only grew faster and louder, sufficiently convincing her that this couldn't be Nate on a return trip. She finally gave in, approaching the metal door and, taking a deep breath, opened it. She tried to slam it shut again when she saw who was on the other side.

"Not now Blair," Jenny said, edging the door shut. "I'm not in the mood."

"Get over yourself little J," Blair said annoyed, as if Jenny was the one bothering her. "I'm not here to do battle."

Jenny finally gave up getting the door shut as Blair had wedged her Italian loafer there, preventing it from closing fully. She let go with a huff and walked back over to her bags, intent on ignoring the brunette if she couldn't get her out of the loft.

"These are Gucci you know," Blair said checking her foot. When she was convinced they were scuff-free she walked further in, trying to keep the disgust at being in a Brooklyn apartment off her face. Instead she turned her attention to Jenny's appearance.

"Rough night?" she asked. When Jenny turned to glare at her, she was able to take in more of how disheveled the younger girl looked. "Make that rough week." She added.

Jenny was not amused. She was late, exhausted and now totally annoyed. "What do you want Blair? Dan isn't here…and besides, I'm pretty sure he hates you." Jenny knew that last part wasn't true but it didn't stop her from saying it.

Jenny was pretty sure she saw Blair wince but she recovered quickly.

"I'm not here to see Hum— your brother," she said. "I'm here to see you. There are a few things we need to get straight." She finally took a moment to glance around the room, noting the boxes and Jenny's bags. "So you're actually going through with it, huh?

Jenny sighed. "Yes! I'm 'going through with it.' Why is that so hard for everyone to believe?"

Blair raised an eyebrow at Jenny's outburst. "I'm not surprised at all," she said.

"You're not?" Jenny asked.

"No," Blair said matter-of-factly. "It makes perfect sense. It's exactly what I would do."

"Really…" Jenny said. Now she was suspicious. If there was one person she could confidently say she didn't share the same thought process with it was Blair Waldorf. "How so?" she asked.

Blair smirked. "You know, running away from something real because you're scared."

Jenny blanched. "What are you talking about?" she asked. "I'm not running away from anything. Besides," she added, "you're the one who threatened my life if I ever came back to New York in the first place."

"And that didn't stop you did it?" Blair said snidely.

"Blair." Jenny said tiredly. "What do you want?"

Blair was quiet for a moment. It was clear that she had something to say but didn't want to say it.

Jenny wasn't exactly feeling patient. "Fine," she said. "Then if you'll excuse me, I have a cab on the way to take me to the train station." She opened the door and waited for Blair to leave.

"Alright," Blair said begrudgingly. "You don't have to be so dramatic." She took another pause, mulling over what she wanted to say. Jenny tapped her foot impatiently.

"I may have been wrong…slightly…in the way I handled things with you. And Chuck." She looked down at her feet before adding, "And Nate for that matter."

Jenny just looked at her. What did she mean Nate?

"Not that you weren't completely tactless for sleeping with Chuck, but I realize that it was my own problem with him and our relationship that really destroyed me. You were just the straw that broke the camel's back."

Jenny was silent, deciding it was better to let Blair get it all out before chiming in.

"Playing games, hurting people who hurt me first, it's the only thing I know. I couldn't believe that you made a mistake. It was easier for me to see it as you trying to humiliate me. That's why I wanted to humiliate you right back."

Now Jenny was starting to get it.

Blair continued, "When I realized what was going on between you and Nate, I had to ruin it, just like I felt you ruined things between me and Chuck. Only, things were already ruined between us, before you two even happened. I just couldn't see it."

"So what changed your perspective?" Jenny asked.

Blair smiled, but only slightly, and in a sort of ironic way. "Your brother."

Jenny smiled too, "Yeah," she said. "He has a way of doing that."

"Anyway," Blair said, shaking her head. "I didn't really need to ruin things between you and Nate because you're doing that all on your own."

"You have no idea what you're talking about Blair," Jenny said.

"Oh, of course I do little J." Blair said. "I'm older, wiser, not to mention more fashionable than you are. But that's beside the point. The fact of the matter is, I've been watching you and Nate dance around each other since he was my boyfriend." She paused. "Come to think of it, you do have a nasty little habit of going after my leftovers." Blair shot Jenny a menacing smirk.

"Nate and I don't work," Jenny said, ignoring Blair's last comment. "Him not wanting me is why things ended up the way they did last year."

"No." Blair argued. "You're why you ended up like you did last year Jenny." Jenny was about to interrupt but Blair kept going. "I know what it's like, you know. How intoxicating it can be, this world we live in. If you aren't raised in it, it can ruin you. That's why Chuck and I always fit so well together, we were both cut from the same dark, power-hungry cloth. But not Nate, never Nate. Sure, he's privileged, but there's something more in him. Something good. He's the kind of person who makes you want to be better."

"We're too different." Jenny said softly.

"Sometimes different is exactly what a person needs," Blair said. "And if you run from it, you'll never really know will you?"

Jenny was pretty sure Blair wasn't just talking about her and Nate but she didn't chance asking her about it. The buzzer by the door rang, alerting her that the cab was here.

"I should go," Jenny said.

"Right," Blair said walking towards the door. "I need to be getting to the spa anyway. It'll take hours to get all of this Brooklyn smog out of my hair."

"Yeah," Jenny said, rolling her eyes. Just as Blair stepped into the hall she added, "He doesn't hate you, you know? I don't think he ever could."

Blair paused at this, then pushed her oversized sunglasses onto her face. "Tell anyone about this and I'll deny it," she said, turning on her heel without so much as a goodbye.

Jenny smirked and stepped back into the loft. She took one last look around before scooping up her bags and closing the door behind her.

* * *

><p>"Just remember you can call me anytime, okay?" Rufus said into Jenny's hair, as he hugged her for the fourth time. They were standing on the platform saying their goodbyes, most of Jenny's bags already on board.<p>

"I know dad, I will." Jenny looked at her father. "You're okay with this right? With me going?"

Rufus smiled. "All I've ever wanted is for you to follow your heart sweetie. And if your heart is telling you Chicago is where you're supposed to be, then yes, I'm more than okay with it."

Jenny smiled, although she was slightly unnerved by what her father said.

"Alright, okay. Don't hog all the goodbyes dad." Dan said, playfully shoving between Jenny and Rufus and giving his sister a hug.

"Love you Jen," he said, squeezing her tightly.

"I love you too Dan," Jenny said. She stayed close to him as they broke apart and whispered, "I hope you can work things out with Blair. She might be the kind of different that you need."

Dan smiled slightly but gave his sister a quizzical look. Jenny just gave him a wink and motioned like she was rocking a baby, which made him laugh. There had been too many serious moments that day to end on such a dramatic note.

"Last call for Brooklyn to Chicago," was announced over the intercom.

"Guess that's my cue," Jenny said hugging her dad and brother each one more time. "Love you," she said, waving as she boarded the train.

Once she was in her seat, she took a deep breath and closed her eyes. While she was already missing New York she started making a mental list of all the things she couldn't wait to get back to in Chicago. This was the right thing, she was sure of it.

* * *

><p>Nate had been walking around the city for three hours. He had all of this emotion penned up inside of him and all he could think to do was…walk. Although at first he had seriously considered drinking himself into oblivion. However, he was pretty sure that would leave him feeling even more useless than he already did so he opted for wandering around aimlessly.<p>

He had been passing the Clock Tower Building on Broadway when he noticed it was 5:30…Jenny's departure time. Realizing she was on her way out of the city took all of the fight he had left out of him and he decided to head home for the night.

When he got back to the hotel, the lobby was empty. Most of the patrons were either already out or getting ready in their suites. Nate decided to just keep his head down and precede straight to the elevator but he was stopped by the concierge.

"Good evening Mr. Archibald." he said. Nate nodded a greeting. "Russell Thorpe's assistant arrived a few moments ago needing to see you. I told her she could wait for you by the fireplace and I would direct you to her when you arrived."

Nate sighed. He was not in the mood to deal with his father's associates right now.

"Look, Peter, I've had a rough day. Could you just tell her to contact my father at his office tomorrow?"

"That isn't the way I would expect the youngest member to ever sit on the Archibald Executive Board to handle a visitor."

Nate froze, recognizing the voice. He turned around slowly and saw Jenny standing behind him. Her cheeks were flushed from the cold, her hair was a mess and she had her carry-on bag in her hand.

Nate just stared at her, almost not believing she was really there.

Jenny knew she wasn't much for finding the perfect words so she just shrugged her shoulders and said the first thing that came to her mind.

"I can't stand deep-dish pizza."

At first, she didn't think Nate was going to react but a second later he moved towards her, quick and fluid, catching her face in his hands and kissing her with everything in him. She smiled against his lips and clutched his shirt in her hands, deepening the kiss.

When Nate finally pulled back, they were both out of breath. He brushed a piece of hair out of Jenny's eyes and smiled down at her.

"This is that moment," Jenny said. "The one that the last three years have all been leading up to."

"Yeah?" Nate asked. Jenny nodded. "Then I guess we better make it count." He lifted her off her feet in another kiss and swirled her around before setting her feet back on the floor. "I love you Jenny," he said softly.

"I know." Jenny replied. "Always have, always will."

THE END.


End file.
